Statement I: In the above reaction, product formed will be a mixture of benzyl alcohol and iodobenzene. Statement II: In the above reaction, the -O-CH₂- bond is cleaved to give the product.
In the light of the above statements, choose the correct answer from the options given below:
(A)Both Statement I and Statement II are true
(B)Both Statement I and Statement II are false
(C)Statement I is true but Statement II is false
(D)Statement I is false but Statement II is true✓ Correct
Answer: (D)
Solution
Protonation of the ether oxygen of benzyl phenyl ether by HI is followed by iodide attack at the benzylic carbon, because that carbon supports a far more stable carbocation-like transition state than the aromatic carbon and the aryl−oxygen bond is never cleaved. The O−CH2 bond therefore breaks, giving phenol and benzyl iodide rather than benzyl alcohol and iodobenzene. The statement about benzyl alcohol and iodobenzene is false while the statement that the O−CH2 bond is cleaved is true.
JEE Main · 2026 · 06 Apr 2026 · Shift 2 · Single correct option
